Have you ever tried to play a “homeless” Sim?

Yes, one of my favorite sims to play starts out as a homeless teen. Similar to the post above, I put him on a plot of land and take away the remaining money. I have him fish or collect things until he can afford to buy a tent, solar shower, cooler, so forth. He sleeps on a bench for the first few days. He'll eat the fruit or veg he harvests, or buys things from a food stall if he can afford it. He also dumpster dives. Sometimes I send him to the humor & hijinks festival and put him on the mischief team. If they win, I have him sell the fireworks and doll. He is also a kleptomaniac, so the mischief helps him build up enough skill to start swiping items. At some point between selling off the things he finds or steals I build him a little shack on his land and he also furnishes his house with the things he finds. He struggles a lot in the beginning but things eventually get better for him. Oh yes, he did get struck by lightning by running around during a storm instead of going into his tent and died but I exited without saving for that. Dumpster diving is what really brings in the bucks.